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Dustin, Mac Support Specialist
Category: Mac
Satisfied Customers: 13305
Experience:  Over a decade putting the missing byte back into Apple. Also worked in The US Army as A Network Switching Systems Operator/Controller
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Mac Mail is making me crazy. I do prefer to use it (as opposed

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Mac Mail is making me crazy. I do prefer to use it (as opposed to another mail program) but ever since I upgraded to OS 10.9, it is acting very quirky. For starters, I have 9 mail accounts connected to it and every time I sit down it gives me pop ups asking me to input my password XXXXX each. Then when I do put in the correct password, it will often still show the account as being offline. My main personal email is YAHOO. I have it set up to go through mac mail. But every day or so it will just suddenly disconnect as well. If I try to send an email it will show the status bar going half way then pop up again and tell me there is no connection. Usually if I restart the program (or my computer) it will fix it. Is there a way to debug this program? What could be causing all of this. It is going to make me CRAZY if I have to enter 9 different password XXXXX time I sit down!!!!
Welcome, my name is XXXXX XXXXX I will assist you today!

We should have a look at this link first, and check and see if it helps.

If that doesnt help, you could try resetting your local items / keychain.. Heres how.

  1. Open 'Keychain Access' Application
  2. Select the 'login' keychain from the keychains list
  3. Click the lock at the top to lock the login keychain
  4. Click the lock again to unlock the login keychainunlock.png
  5. After entering your login keychain password XXXXX should be presented with a dialog:reset.password.png
  6. Clicking the reset button will re-sync your login.keychain password XXXXX the iCloud keychain password.

If everything from the above fails for whatever reason the last resort you can do the following:

  1. Open terminal
  2. cd ~/Library/Keychains
  3. ls
    1. When you 'ls' here you will see a folder that contains a bunch of random number liks so:
    2. 94ED610F-DD96-4ECF-A2BC-7D2F8651A464 (this number is XXXXX on each system)
  4. rm -rf 94ED610F-DD96-4ECF-A2BC-7D2F8651A464
  5. Reboot
  6. <when you log back in everything should be back to normal>


If those steps dont get mail to accept the passwords, and save them.( you may have to enter the password XXXXX each email account one more time )


Then send a reply and let me know so that we can continue working the issue together..



I strive to provide great service, and greatly appreciate a rating of excellent below when you are satisfied.. I always answer follow up questions.

Dustin S.

Senior Technician and Network Switching Systems Operator / Maintainer.

Dustin and 3 other Mac Specialists are ready to help you
Customer: replied 3 years ago.

Cool. Thanks. Give me a few hours to test all of this out. Will get back to you later today or tomorrow morning.

Hello again Sean.

Just wanted to touch base with you today to see how you fared.. If you ran into any issues with the previous steps, I can help you complete them. Or, if you were able to complete the steps and the problems are still happening, then we can try more steps as needed.

Customer: replied 3 years ago.
Hi. I tries the first step of rebooting the keychain, but it didn't do much. Will keep going down your list this morning and get back to you ASAP. It Saturday and with two little kids it is hard to find a quiet moment to work on this ;). Thanks for being patient
Not a problem Sean.. And believe me, I understand it being the ifrst day of the weekend and wanting / needing to attend to the little ones.

Take your time, if you run into any issues send a reply and let me know what they are so I Can help you with them.. and please dont feel pressured on time.. Theres no expiration date on this session or my ability to help with this.

Dustin S.